


Everything On The Rack

by hehkhatea



Series: Widojest Week 2k20 [2]
Category: Critical Role (Web Series)
Genre: F/M, First Dates, Fluff, Gift Giving, Shopping, Zip Me Up Trope
Language: English
Status: Completed
Published: 2020-07-08
Updated: 2020-07-08
Packaged: 2021-03-04 18:40:57
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,176
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25141045
Author URL: https://archiveofourown.org/users/hehkhatea/pseuds/hehkhatea
Summary: Jester and Caleb are going to have their first date and need new goin' out outfits.title comes from "I Don't Want It At All" By Kim Petras
Relationships: Jester Lavorre/Caleb Widogast
Series: Widojest Week 2k20 [2]
Series URL: https://archiveofourown.org/series/1819591
Kudos: 29





	Everything On The Rack

Jester was fully aware that Caleb was not the most fashionable person out there. When given the time and comfort to shop for clothes, he can come out looking fairly decent. He used to dress… modestly, is perhaps the nicest way for her to describe it. She knows why he dressed the way he did, but it still made her feel kind of sad to think about. But now-

“ _Cayyyleeeeb_...” Jester groaned, dragging her nails down her face. “These shirts look almost exactly the same!”

Caleb winced, glancing at Jester and frowning. She knew he tended to agonize over choices, and sometimes it was cute. His thought process always reflected on his face; the crease between his eyebrows, the quick jumps his intense blue eyes do as if he's drawing spells with them. 

However, this was one of those times when Jester was feeling just a little bit more impatient than she probably should be. She was still working on it, especially with Caleb, but to her credit, she’d been letting him look at these two black tunics for almost five minutes. She had her limits. They hadn’t been in this particular clothing shop for very long, but there were only so many hours in a day.

“They are not that similar, Jester.” Caleb defended, though the tone in his voice didn’t seem all that forceful. “This one has an asymmetrical collar at a more severe degree than this one. And while this one is an onyx black, the other is more of a charcoal.” 

This had to be a joke, there was _no way_ Caleb was _serious_.

“Jester,” Caleb sighed, defeated. “You should probably go back to the house, I don’t want to bore you more than I already am.”

“But I want to help you, Cayleb!” Jester grabbed his hand. “You said you wanted our first date to be unforgettable!”

“Ja, but that doesn’t really mean much to me, I don’t forget anything.” Caleb’s face grew a bit red as he cleared his throat. “I think no matter what, I wouldn’t forget…”

Oh _Traveller_ , Caleb was _good_. Out of practice, he had said. Yeah, right! Jester’s heart fluttered like a bird in a cage, or more accurately like an albatross but that's semantics.

“Ooh!” Jester felt her own face heat up under the hand she pressed to her cheek. “You can’t just say something sweet like that, Cayleb!”

“Nein?” Caleb said, almost sincerely. 

“Neeeinn,” Jester replied. “I’m going to get a toothache if you keep this up!”

Caleb chuckled quietly, and Jester had to look away before she got any ideas having to do with other nice sounds she could have Caleb make.

Looking around the shop, Jester’s eye caught onto something white and airy. She practically skipped over to the billowing poet’s shirt that had little string ties that closed up the opening in the chest. It didn’t have ruffles but it sure wasn’t the most opaque of shirts. Jester wiggled her eyebrows at Caleb as she held the shirt up for him.

“Hmm,” Caleb squinted his eyes in mock suspicion. “I think I know _exactly_ why you’d want me to wear that.”

“Why?” Jester grinned.

“Might it have something to do with that smutty book you purchased the other day?”

_The Day The Pirates Came_ did happen to have a super hot man on the cover that just _happened_ to have a shirt that looked just like the one that Jester was holding, but _everyone_ wore shirts like this. Well, everyone but Caleb. Unless…

“Ooh!” Jester jumped a little. “Cayleb, I just thought of a really cool idea!” Caleb raised one of his eyebrows, with interest rather than doubt. “What if _I_ buy _your_ outfit for our date, and _you_ buy _my_ outfit?”

Caleb pressed his lips together in thought. Jester shimmied her shoulders a little, causing the jeweled fringe of her coat to shake.

“You did pick out something nice for me at that ball…” Caleb reasoned, his voice low as if he was still thinking it over. “But I would not put it past you to make me wear something ridiculous.”

“I promise I will pick something very handsome for you, Cayleb.” If she really wanted him on her side, she’d have to bring out the big guns. She made her little eyebrows knit upward, her eyes widened more maximum cuteness, and gave the sweetest lil pout she should muster.

Caleb-puddy, meet Jester’s hand.

* * *

Okay, picking out clothes for Caleb _was_ a lot harder than Jester thought. At least last time she had Caduceus with her and Caduceus was a bit more sensible when it came to clothing. But when Jester was all by herself her mind began to run wild with scenarios of what Caleb would look like with every piece of clothing she came across. It still took her about an hour to put together his whole outfit.

She was, however, stunned when she came back to the house and saw that whatever Caleb had picked out for her was already there. A dress box sitting on her bed. She had placed Caleb’s clothes on the desk in his study but couldn’t find him anywhere.

Jester could never resist a present, and it was true agony to try and convince herself that she should wait until tomorrow to open it. One peek wouldn’t hurt, right? Opening one side of the box, she saw a layer of tissue paper but just below that was the barest hint of lavender. Lavender! Was that his favorite color? Oh right, Caleb didn’t have a favorite color.

So, now she just had to wait until tomorrow night to wear it… Easy… 

Jester opened the box again and made a more thorough investigation of the dress. It looked to have a sort of sweetheart neckline with loose straps that are meant to hang off the shoulders. Pearls and small gems were sewn into the fabric by the neckline. The bodice gave the illusion of visible boning as if she was wearing a corset on the outside. How much had Caleb spent on this? It seemed rather luxurious.

It almost made Jester feel bad that all they were doing for a date was seeing a play. She supposed people dressed up to go to the theater but what Jester had picked out was not nearly as fancy as this. She didn’t know why she was feeling so self conscious of this, she should feel elated at the thought and care Caleb put in for this. Jester did feel those things, but now she was worried he’d gone overboard, or that she hadn’t done enough.

Jester’s fingers stroked the silky fabric of the dress, it felt cool and soft and it had almost a metallic effect when she moved it in a way. Oh no, she was already falling in love with the dress. It was one of the nicest things someone has ever given her, and it was extra nice that it was from Caleb.

Putting the lid back on the box, Jester put the thing under her bed, hoping that for a while she’d resist the urge to take it out just to look at it.

* * *

If only the dress didn’t have ties in the back. Everything fit just fine but she couldn’t actually finish putting on the dress because she could not tie it up in the back. Jester almost felt like crying, it was so unfair that so much of the dress was so good and so beautiful but the gods damn TIES. She tried her best to reach behind herself but she was worried about the string of pearls that hung delicately from the straps breaking.

Normally, she could ask anyone in the house for help, except that everyone, sans Caleb, was already gone.

“Jester,” She heard Caleb’s voice on the other side of the door as he knocked. “Are you ready?”

“No…” She groaned. “I can’t get the back.”

“Do you…” The sound of him clearing his throat was muffled through the door. “Do you want me to help?”

“It will ruin the surprise!” Jester complained.

“I already know what the dress looks like, Jester.”

“Yah, but you haven’t seen me in it!”

“Jester, if I don’t help you we will be late.”

Jester sighed. This really wasn’t going at all like she was hoping, she wanted to make a grand entrance going down the stairs and for Caleb to be standing at the bottom of them and for him to look up at her and go “wow Jester you look beautiful”. That’s always how it went in books, at least. Reluctantly, Jester went to the door and opened it for Caleb.

He was fiddling with the sleeve of his coat, the coat Jester got for him. It was a smokey grey color that made his shoulders look broader and had a high collar that led to pointed lapels across his chest. A ruffled white cravat was tied impeccably spilled out from his jacket. He was wearing his usual boots but it looked like he had shined them. Maybe Jester had accidentally gotten the measurements for his pants a bit wrong because they looked much tighter than expected… maybe, accidentally. Who knows!

In any case, Jester did a damn fine job of making Caleb look good, but perhaps the best part of his look was that his hair was down. She knew that his hair had gotten longer over the months, it was evident with the fact that he tied it up, but rarely did she ever see it down. And that, all together, caused Jester’s jaw to drop.

“Oh Cayleb,” Jester breathed. “You look so handsome!” Jester had clearly outdone herself, all that time worrying was for nothing. But Caleb stood very still, and was very red. Jester looked down, worried that maybe she had accidentally flashed him or something. The dress was hanging loose on her but nothing was _out_.

“Cayleb,” Jester said, trying to get his attention. He blinked, then blinked again, and he looked back at Jester.

“Sorry, ja, I’m here.” Caleb ran his hand through his hair. “Uhm, You ah, need me to tie you in?”

Oh, Caleb was checking her out. That was new.

“Yes, please!” Jester let Caleb into her room and stood in front of the floor length mirror. The lazy straps of the gown hung over her biceps and the curved neckline looked like a mountain range of taffeta and pearls and gems. She wore a cinch underneath the dress to give the full effect of an hourglass waist as the dress fanned down to her shins. Jester didn’t want to admit to herself that it might be better than the one she had gotten for herself for the ball but she had to hand it to Caleb, she looked gorgeous.

Standing behind Jester, she saw Caleb approach her and gingerly pull at the ties.

“Do you want it very tight?” Caleb asked, looking at her through the mirror. His voice was almost a whisper. A purple blush spread over Jester’s freckled cheeks.

“A little.” Jester replied. She held onto her diaphragm to let the dress fit as best as it could. She felt his deft fingers loop through the stays, felt the dress close and tighten in the back, the dress conforming to her body. The barest hint of Caleb’s breathing through his nose tickled the back of his neck, sending a shiver down her spine.

“Does that feel alright?” Caleb’s hand touched between her shoulder blades. “Not too tight?”

Jester couldn’t help but think about how intimate these questions came out. This sounded more like questions someone would say during-

“No,” Jester smiled. “It’s perfect!”

“Are you sure?” Caleb clarified. “You looked a bit-”

“I was just thinking…” Jester bit her lip, trying to keep herself from laughing. Caleb shook his head, accepting defeat and understanding what she was going on about.

Looking at them both in the mirror, Jester thought they both looked rather good. The cool color of Jester’s skin matched well with the muted purple, the sparkles paralleled her glittery diamond tattoo. Caleb might not fully look like a smutty romance cover model but he did have the air of a romantic lead.

They just stared at each other through the mirror for a moment. Smiling, breathing. Caleb’s hand snaked around her waist, putting it over where Jester’s was.

“I don’t know what word to use to describe how you look, Jester.” Caleb said before he kissed the back of Jester’s head. “There’s too many synonyms for beautiful.”

Jester chuckled, squeezing Caleb’s hand that was placed below her chest. “Thank you, Cayleb.”

There was uncertainty between them, Jester kind of wanted to do something. Wanted to turn around. Wanted to get on her tiptoes.

“We’re going to be late.” Caleb reminded, stepping away from Jester. Letting go of her hand. Jester turned around and saw Caleb was offering his elbow to her. “Shall we?”

Grinning, Jester put her hand over his arm. “We shall!” She replied.

**Author's Note:**

> wasn't totally inspired by the prompt but shout out to ellen for giving me the idea of them shopping together/for each other!


End file.
